Holiday rentals with a pool in Pensacola Bay

Hot tub/ Pool Relaxing Getaway

Picture your family enjoying the pool & hot tub while you grill out in the large private backyard, or lounge in the comfy screened in porch seating area of this peaceful getaway! Located b/t the bayou & scenic bluffs overlooking the bay, our home is close to all the area has to offer! Relax on the beach, visit the fishing pier or historic downtown's upscale dining/shopping. 1 block from Exchange Park which has baseball/softball fields, a playground, free wifi, walking path/trails & picnic areas!

Private Pool-Near NAS-Grills-Game Room FamilySetUp

You have found a home that is loved by so many who come to Pensacola! This home offers so much for families: arcade room, board games, foosball coffee table, cards, the pool, it's full of fun! Guests rave about how clean it is, that pics are accurate & how quiet the neighborhood is yet a simple drive to restaurants, attractions and the beaches. Great for visiting military at NAS/Corry station or events as kite fest, wahoo games, bands on the beach, theater, Friday art nights and parades! BookNow

Our Shangrila: Waterfront Home with Kayaks & More

Welcome to Our Shangrila! This home sits directly on a calm, shallow cove of Perdido Bay, providing the perfect place for families to relax, play, swim, & paddle safely. Come enjoy gorgeous views, coffee on the balconies, & serene waters. This 2 bed/2.5 bath sleeps up to 7 & includes a full kitchen, laundry, 2 kayaks, 2 SUPs, & more! Spend all day right here, isolated from the hustle & bustle. Or take a very short drive to the beaches, dining & more along Perdido Key. Continue for more Details

Funky Flamingo~ Guest House~ Pool & Kitchenette

This charming East Hill pool bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & entire back yard. Luxury comforts and amenities, with the highest speed Wi-Fi/streaming services. Casper mattress and pillows with (700 thread count Egyptian Cotton sheets), for an amazing nights rest. Beach chairs, cooler, umbrella and towels provided. Enjoy the new walk-in shower w/ tankless hot water heater. LBGTQIA2S+ friendly!

Vintage Charmer with Tiny Pool Close to Downtown

Great historical Pensacola home with vintage charm & modern comfort. Our favorite part is the Beautiful Kitchen and private Backyard! Enjoy the gas BBQ grill out on the deck or chill in the hammock underneath the palm trees. A welcoming space to spend time with family & loved ones. Enjoy a fun unique atmosphere with a mix of new & vintage furniture & art. Convenient location close to Downtown Palafox Pier, Pensacola Bay Center, NAS Navy Base, local area hospitals, 15 mins from Pensacola Beach.

Historic Downtown Bayfront Home Pool Mins to Beach

The Bayfront Manor brings the best of both worlds to your vacation or business stay in Pensacola. Located 5 min walk from historic downtown, Seville Square, and Palafox Street, the location is ideal for all dining, nightlife, and events. The home is positioned on the corner of Bayfront Dr allowing for great water views of Pensacola Bay. The best beaches on the Gulf are only a 10 min drive. The location is also great for wedding parties as the Barkley House and Christ Church are walkable.

Newly renovated condo with amazing water views!

Experience the clear blue water and white sand of Pensacola Beach. Enjoy spectacular views of Pensacola Bay from a private 3rd floor balcony. This newly renovated condo offers solid surface floors throughout, a fully stocked kitchen and calming beach decor. The master has a queen size bed, flat screen TV, and ensuite bathroom. The 2nd bedroom offers 2 full size bunk beds. The main living room has another flat screen TV, comfortable couch and is a perfect place for your group to gather.

Sunset on the Bayou near NAS/Downtown Pensacola

If you’re looking for a quiet get-away on the water, you will find it here. Our cozy 2 bed/2 bath condo is like a cottage by the sea in a condo setting. Relaxing coastal decor and a beautiful view from the balcony make our home enjoyable inside and out. Enjoy all the amenities of home, sunbathe by the pool, fish from the dock, relax on the balcony, grill out on the lawn. Its all here. Just a short drive from Pensacola NAS, Pensacola Beach and historic Downtown Pensacola. (No pets allowed)

Private Pool / Two living rooms /Downtown

This 3000sqft home features a private pool, two living rooms, four bedrooms, two bathrooms, a kitchen, and a beautiful sunroom overlooking a private pool! Two families traveling together?? This is the ideal home for you! This home sleeps 10 comfortably but can accommodate more with the use of an air mattress or crib if traveling with a toddler. Located just a few blocks from Joe Patti's, the Blue Wahoo Stadium, and Palafox Street! YOU AGREE TO ALL HOUSE RULES WHEN YOU BOOK. READ THEM.

Beachfront Condo • Pool & Resort Perks

Welcome to Pensacola Perch, an 8th‑floor beachfront condo offering expansive views of Pensacola Beach—perfect for dolphin watching and catching the Blue Angels airshow. This modern 2BR/2BA condo sits in the highly sought‑after Emerald Isle gated resort, where guests enjoy premium amenities including direct beach access, two swimming pools, a hot tub, sauna, and a beachfront fitness center. From March–October, enjoy complimentary beach chairs and an umbrella from La Dolce Vita.

Bliss on the Bay 2BR 2BA Beach Condo with Pool D7

Relax with family or friends at our cozy condo with amazing views of the bay and the Gulf of Mexico. You are mere steps from the gulf's famous sugar white sandy beaches. Enjoy the complex's amenities- sun at the private beach, swim in the pool (unheated), grill on the BBQ and chill at the fire pit. Rent bikes and explore the miles of beach paths and the Fort at Pickens. You're a short drive to the core of the beach where there's shopping, restaurants, bars and family activities.

Beautiful 1-bedroom cottage with pool

This rental is located near Navy Point - minutes to NAS, Boating Marinas, and Downtown Pensacola and only a short 20 minute drive to the white sand beaches of Pensacola or Perdido Key. This home features an above ground pool, screened in porch, patio and grill. This rental is the perfect place to relax and unwind after a day at the beach or exploring Pensacola and it's surroundings.